# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mo_wesley_unknown1_0m _database_code_depnum_ccdc_archive 'CCDC 828908' #TrackingRef 'mo_Wesley_unknown1_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N O5' _chemical_formula_weight 317.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.215(13) _cell_length_b 7.397(7) _cell_length_c 16.759(15) _cell_angle_alpha 90.00 _cell_angle_beta 111.05(2) _cell_angle_gamma 90.00 _cell_volume 1645(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_T_max 0.9632 _exptl_absorpt_process_details multiscan _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14451 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3761 _reflns_number_gt 2573 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.3216P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.008(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3761 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C8 C 0.39608(12) 0.2847(2) 0.31725(11) 0.0439(4) Uani 1 1 d . . . C1 C 0.44059(12) 0.2397(2) 0.45951(10) 0.0411(4) Uani 1 1 d . . . C7 C 0.50869(11) 0.3112(2) 0.35737(10) 0.0392(4) Uani 1 1 d . . . C6 C 0.53167(11) 0.2826(2) 0.44853(10) 0.0384(4) Uani 1 1 d . . . C5 C 0.61820(12) 0.2887(2) 0.51951(10) 0.0466(4) Uani 1 1 d . . . H5 H 0.6796 0.3160 0.5143 0.056 Uiso 1 1 calc R . . C2 C 0.43486(14) 0.2059(3) 0.53820(11) 0.0540(5) Uani 1 1 d . . . H2 H 0.3738 0.1782 0.5440 0.065 Uiso 1 1 calc R . . C3 C 0.52274(15) 0.2145(3) 0.60804(12) 0.0586(5) Uani 1 1 d . . . H3 H 0.5212 0.1935 0.6623 0.070 Uiso 1 1 calc R . . C4 C 0.61322(14) 0.2536(3) 0.59909(11) 0.0545(5) Uani 1 1 d . . . H4 H 0.6719 0.2565 0.6473 0.065 Uiso 1 1 calc R . . C10 C 0.67256(13) 0.3724(3) 0.33550(12) 0.0517(4) Uani 1 1 d . . . C9 C 0.56200(12) 0.3488(2) 0.30659(10) 0.0432(4) Uani 1 1 d . . . C11 C 0.51146(13) 0.3804(3) 0.21223(11) 0.0496(4) Uani 1 1 d . . . C12 C 0.25757(12) 0.1904(3) 0.36656(12) 0.0533(5) Uani 1 1 d . . . H12A H 0.2568 0.0958 0.4064 0.064 Uiso 1 1 calc R . . H12B H 0.2263 0.1427 0.3091 0.064 Uiso 1 1 calc R . . C13 C 0.19650(15) 0.3485(3) 0.37766(18) 0.0820(7) Uani 1 1 d . . . H13A H 0.2261 0.3945 0.4349 0.123 Uiso 1 1 calc R . . H13B H 0.1287 0.3099 0.3675 0.123 Uiso 1 1 calc R . . H13C H 0.1959 0.4419 0.3377 0.123 Uiso 1 1 calc R . . N1 N 0.36207(9) 0.23840(19) 0.38070(9) 0.0451(3) Uani 1 1 d . . . O1 O 0.34564(9) 0.2992(2) 0.24221(8) 0.0615(4) Uani 1 1 d . . . O3 O 0.70339(9) 0.36872(18) 0.26960(8) 0.0589(4) Uani 1 1 d . . . O2 O 0.72790(11) 0.3936(3) 0.40654(9) 0.1004(7) Uani 1 1 d . . . O4 O 0.49211(11) 0.5300(2) 0.18256(9) 0.0710(4) Uani 1 1 d . . . O5 O 0.49908(10) 0.22654(18) 0.16822(8) 0.0586(4) Uani 1 1 d . . . C16 C 0.4532(2) 0.2419(4) 0.07604(13) 0.0824(7) Uani 1 1 d . . . H16A H 0.4090 0.3463 0.0615 0.099 Uiso 1 1 calc R . . H16B H 0.4128 0.1353 0.0532 0.099 Uiso 1 1 calc R . . C14 C 0.80981(15) 0.3873(3) 0.28616(15) 0.0752(6) Uani 1 1 d . . . H14A H 0.8466 0.2884 0.3218 0.090 Uiso 1 1 calc R . . H14B H 0.8346 0.4999 0.3160 0.090 Uiso 1 1 calc R . . C15 C 0.82527(19) 0.3856(4) 0.20301(17) 0.0883(8) Uani 1 1 d . . . H15A H 0.8037 0.2714 0.1752 0.133 Uiso 1 1 calc R . . H15B H 0.8954 0.4032 0.2128 0.133 Uiso 1 1 calc R . . H15C H 0.7866 0.4810 0.1673 0.133 Uiso 1 1 calc R . . C17 C 0.5316(2) 0.2610(4) 0.03672(16) 0.1049(10) Uani 1 1 d . . . H17A H 0.5706 0.3680 0.0584 0.157 Uiso 1 1 calc R . . H17B H 0.4995 0.2700 -0.0243 0.157 Uiso 1 1 calc R . . H17C H 0.5750 0.1572 0.0507 0.157 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C8 0.0344(8) 0.0522(9) 0.0402(9) -0.0029(7) 0.0074(7) 0.0016(7) C1 0.0350(8) 0.0441(8) 0.0408(9) -0.0019(7) 0.0093(7) -0.0004(6) C7 0.0329(8) 0.0424(8) 0.0386(8) -0.0031(6) 0.0082(6) 0.0023(6) C6 0.0353(8) 0.0393(8) 0.0374(8) -0.0036(6) 0.0094(6) -0.0004(6) C5 0.0361(8) 0.0561(10) 0.0426(9) -0.0030(7) 0.0079(7) -0.0027(7) C2 0.0452(10) 0.0699(12) 0.0472(10) 0.0048(8) 0.0170(8) -0.0055(8) C3 0.0574(11) 0.0758(13) 0.0402(10) 0.0065(9) 0.0147(9) -0.0025(9) C4 0.0462(10) 0.0678(12) 0.0390(10) 0.0010(8) 0.0025(8) -0.0014(8) C10 0.0417(9) 0.0691(12) 0.0457(10) -0.0039(8) 0.0174(8) -0.0032(8) C9 0.0388(8) 0.0487(9) 0.0409(9) -0.0031(7) 0.0128(7) 0.0025(7) C11 0.0425(9) 0.0616(11) 0.0452(10) 0.0037(8) 0.0162(8) 0.0034(8) C12 0.0335(8) 0.0628(11) 0.0588(11) -0.0054(9) 0.0109(8) -0.0121(8) C13 0.0398(10) 0.0805(15) 0.124(2) -0.0189(14) 0.0277(12) -0.0041(10) N1 0.0309(7) 0.0580(8) 0.0425(8) -0.0015(6) 0.0086(6) -0.0040(6) O1 0.0395(7) 0.0947(10) 0.0406(7) 0.0010(6) 0.0025(5) -0.0009(6) O3 0.0449(7) 0.0822(9) 0.0559(8) -0.0061(6) 0.0258(6) -0.0049(6) O2 0.0439(8) 0.205(2) 0.0503(9) -0.0138(10) 0.0141(7) -0.0265(10) O4 0.0754(10) 0.0685(9) 0.0629(9) 0.0166(7) 0.0173(7) 0.0137(7) O5 0.0637(8) 0.0692(8) 0.0397(7) -0.0050(6) 0.0147(6) -0.0015(6) C16 0.0856(17) 0.1111(19) 0.0391(11) -0.0067(11) 0.0088(11) -0.0067(14) C14 0.0458(11) 0.1058(18) 0.0820(15) -0.0076(13) 0.0328(11) -0.0073(11) C15 0.0865(17) 0.0966(18) 0.110(2) -0.0167(14) 0.0694(16) -0.0138(13) C17 0.137(3) 0.129(2) 0.0553(15) 0.0076(14) 0.0426(17) 0.0193(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C8 O1 1.208(2) . ? C8 N1 1.361(2) . ? C8 C7 1.510(2) . ? C1 C2 1.373(3) . ? C1 N1 1.390(2) . ? C1 C6 1.408(2) . ? C7 C9 1.356(2) . ? C7 C6 1.458(3) . ? C6 C5 1.371(2) . ? C5 C4 1.385(3) . ? C2 C3 1.372(3) . ? C3 C4 1.378(3) . ? C10 O2 1.178(2) . ? C10 O3 1.327(2) . ? C10 C9 1.479(3) . ? C9 C11 1.502(3) . ? C11 O4 1.204(2) . ? C11 O5 1.333(2) . ? C12 N1 1.461(2) . ? C12 C13 1.507(3) . ? O3 C14 1.443(3) . ? O5 C16 1.449(3) . ? C16 C17 1.490(4) . ? C14 C15 1.487(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C8 N1 126.25(16) . . ? O1 C8 C7 126.15(15) . . ? N1 C8 C7 107.59(14) . . ? C2 C1 N1 127.37(16) . . ? C2 C1 C6 122.77(15) . . ? N1 C1 C6 109.86(15) . . ? C9 C7 C6 136.20(15) . . ? C9 C7 C8 119.29(15) . . ? C6 C7 C8 104.50(13) . . ? C5 C6 C1 118.33(16) . . ? C5 C6 C7 134.26(15) . . ? C1 C6 C7 107.41(14) . . ? C6 C5 C4 119.29(17) . . ? C3 C2 C1 117.43(18) . . ? C2 C3 C4 121.07(18) . . ? C3 C4 C5 121.10(17) . . ? O2 C10 O3 122.93(17) . . ? O2 C10 C9 126.29(16) . . ? O3 C10 C9 110.77(16) . . ? C7 C9 C10 125.88(16) . . ? C7 C9 C11 121.93(16) . . ? C10 C9 C11 112.13(14) . . ? O4 C11 O5 126.25(18) . . ? O4 C11 C9 121.97(17) . . ? O5 C11 C9 111.61(16) . . ? N1 C12 C13 112.85(16) . . ? C8 N1 C1 110.57(15) . . ? C8 N1 C12 124.07(15) . . ? C1 N1 C12 125.34(15) . . ? C10 O3 C14 118.35(16) . . ? C11 O5 C16 116.25(17) . . ? O5 C16 C17 110.9(2) . . ? O3 C14 C15 108.45(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.307 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.032